Synthesis of sugar-lactams from azides of glucuronic acid

Christina Loukou; Manuela Tosin; Helge Müller-Bunz; Paul V. Murphy

doi:10.1016/j.carres.2007.04.003

Synthesis of sugar-lactams from azides of glucuronic acid

Christina Loukou
, Manuela Tosin
, Helge Müller-Bunz
, Paul V. Murphy

Centre for Synthesis and Chemical Biology

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

12 Citations (Scopus)

Abstract

Sugar-lactams have found application as glycosidase inhibitors, synthetic precursors of iminosugars and they are structural components of natural products. The synthesis of β-d-glucopyranosidurono-6,1-lactams from glucuronic acid derivatives are described. NMR data and X-ray crystal structures indicate that the sugar-lactams adopt distorted ¹C₄ conformations in solution and in the solid state.

Original language	English
Pages (from-to)	1953-1959
Number of pages	7
Journal	Carbohydrate Research
Volume	342
Issue number	12-13
DOIs	https://doi.org/10.1016/j.carres.2007.04.003
Publication status	Published - 3 Sep 2007
Externally published	Yes

Keywords

Amides
Glucuronic acid
Glycosyl azides
Sugar amino acids
Sugar-lactams
Sugar-lactones

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10.1016/j.carres.2007.04.003

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title = "Synthesis of sugar-lactams from azides of glucuronic acid",

abstract = "Sugar-lactams have found application as glycosidase inhibitors, synthetic precursors of iminosugars and they are structural components of natural products. The synthesis of β-d-glucopyranosidurono-6,1-lactams from glucuronic acid derivatives are described. NMR data and X-ray crystal structures indicate that the sugar-lactams adopt distorted 1C4 conformations in solution and in the solid state.",

keywords = "Amides, Glucuronic acid, Glycosyl azides, Sugar amino acids, Sugar-lactams, Sugar-lactones",

author = "Christina Loukou and Manuela Tosin and Helge M{\"u}ller-Bunz and Murphy, \{Paul V.\}",

year = "2007",

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doi = "10.1016/j.carres.2007.04.003",

language = "English",

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journal = "Carbohydrate Research",

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T1 - Synthesis of sugar-lactams from azides of glucuronic acid

AU - Loukou, Christina

AU - Tosin, Manuela

AU - Müller-Bunz, Helge

AU - Murphy, Paul V.

PY - 2007/9/3

Y1 - 2007/9/3

N2 - Sugar-lactams have found application as glycosidase inhibitors, synthetic precursors of iminosugars and they are structural components of natural products. The synthesis of β-d-glucopyranosidurono-6,1-lactams from glucuronic acid derivatives are described. NMR data and X-ray crystal structures indicate that the sugar-lactams adopt distorted 1C4 conformations in solution and in the solid state.

AB - Sugar-lactams have found application as glycosidase inhibitors, synthetic precursors of iminosugars and they are structural components of natural products. The synthesis of β-d-glucopyranosidurono-6,1-lactams from glucuronic acid derivatives are described. NMR data and X-ray crystal structures indicate that the sugar-lactams adopt distorted 1C4 conformations in solution and in the solid state.

KW - Amides

KW - Glucuronic acid

KW - Glycosyl azides

KW - Sugar amino acids

KW - Sugar-lactams

KW - Sugar-lactones

UR - https://www.scopus.com/pages/publications/34447336693

U2 - 10.1016/j.carres.2007.04.003

DO - 10.1016/j.carres.2007.04.003

M3 - Article

C2 - 17477912

AN - SCOPUS:34447336693

SN - 0008-6215

VL - 342

SP - 1953

EP - 1959

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 12-13

ER -

Synthesis of sugar-lactams from azides of glucuronic acid

Abstract

Keywords

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